US4132739A - Method for the preparation of carbonyl products starting from hydrocarbon streams coming from steam-cracking installations - Google Patents
Method for the preparation of carbonyl products starting from hydrocarbon streams coming from steam-cracking installations Download PDFInfo
- Publication number
- US4132739A US4132739A US05/702,584 US70258476A US4132739A US 4132739 A US4132739 A US 4132739A US 70258476 A US70258476 A US 70258476A US 4132739 A US4132739 A US 4132739A
- Authority
- US
- United States
- Prior art keywords
- stream
- steam
- alcohol
- cracking
- ions
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 19
- 239000004215 Carbon black (E152) Substances 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000004230 steam cracking Methods 0.000 title claims abstract description 13
- 238000009434 installation Methods 0.000 title claims abstract description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 title abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 32
- 230000002378 acidificating effect Effects 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 150000002500 ions Chemical class 0.000 claims abstract description 11
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 7
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 7
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 13
- -1 olefin hydrocarbon Chemical class 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
- 239000005977 Ethylene Substances 0.000 claims description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 229910052712 strontium Inorganic materials 0.000 claims description 2
- 239000000047 product Substances 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000011347 resin Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229960000834 vinyl ether Drugs 0.000 description 2
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-HQMMCQRPSA-N Ethanol-14C Chemical compound C[14CH2]O LFQSCWFLJHTTHZ-HQMMCQRPSA-N 0.000 description 1
- 229910003556 H2 SO4 Inorganic materials 0.000 description 1
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23K—SOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
- B23K35/00—Rods, electrodes, materials, or media, for use in soldering, welding, or cutting
- B23K35/40—Making wire or rods for soldering or welding
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C07C41/54—Preparation of compounds having groups by reactions producing groups by addition of compounds to unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Definitions
- the present invention relates to a method for the preparation of:
- the hydrocarbon stream (7) is sent to a gas-liquid scrubber column (14) for removing the unreacted alcohol which is possibly present in it (to this purpose, water fed through the main 13 is used);
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mechanical Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25169A/75 | 1975-07-08 | ||
| IT25169/75A IT1039738B (it) | 1975-07-08 | 1975-07-08 | Metodo di preparazione di prodot ti carbonilici a partire da correnti idrocarburiche provenienti da impianti di piroscissione con va pore |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4132739A true US4132739A (en) | 1979-01-02 |
Family
ID=11215899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/702,584 Expired - Lifetime US4132739A (en) | 1975-07-08 | 1976-07-06 | Method for the preparation of carbonyl products starting from hydrocarbon streams coming from steam-cracking installations |
Country Status (28)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100674312B1 (ko) * | 2000-09-08 | 2007-01-24 | 에스케이 주식회사 | 아세틸렌 알코올 화합물의 연속 제조방법 |
| CN104549501A (zh) * | 2013-10-28 | 2015-04-29 | 中国石油化工股份有限公司 | 双醋酸亚乙酯法醋酸乙烯催化剂及醋酸乙烯合成方法 |
| CN104844437A (zh) * | 2015-05-12 | 2015-08-19 | 辽宁省石油化工规划设计院有限公司 | 九塔连续精馏法分离溶剂的方法及其装置 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0740815Y2 (ja) * | 1989-10-20 | 1995-09-20 | シャープ株式会社 | 石油燃焼器の臭気低減装置 |
| JP2537890Y2 (ja) * | 1990-05-09 | 1997-06-04 | パイロットインキ株式会社 | 表面温度表示付ヘアカーラー |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2853520A (en) * | 1953-11-05 | 1958-09-23 | Univ Ohio State Res Found | Conversion of ethynyl compounds to acetyl compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE705273C (de) * | 1937-11-17 | 1941-04-22 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von Acetaldehyd |
-
1975
- 1975-07-08 IT IT25169/75A patent/IT1039738B/it active
-
1976
- 1976-06-25 NO NO762203A patent/NO145336C/no unknown
- 1976-06-25 ZA ZA763796A patent/ZA763796B/xx unknown
- 1976-06-30 AU AU15434/76A patent/AU499973B2/en not_active Expired
- 1976-06-30 YU YU01610/76A patent/YU161076A/xx unknown
- 1976-07-05 DK DK303776A patent/DK303776A/da not_active Application Discontinuation
- 1976-07-06 CS CS764464A patent/CS194768B2/cs unknown
- 1976-07-06 LU LU75310A patent/LU75310A1/xx unknown
- 1976-07-06 TR TR18854A patent/TR18854A/xx unknown
- 1976-07-06 US US05/702,584 patent/US4132739A/en not_active Expired - Lifetime
- 1976-07-06 GB GB28111/76A patent/GB1535288A/en not_active Expired
- 1976-07-06 IN IN1194/CAL/76A patent/IN144393B/en unknown
- 1976-07-06 DD DD193729A patent/DD125067A5/xx unknown
- 1976-07-06 ES ES449924A patent/ES449924A1/es not_active Expired
- 1976-07-07 AT AT498576A patent/AT348977B/de active
- 1976-07-07 CH CH872776A patent/CH624084A5/it not_active IP Right Cessation
- 1976-07-07 NL NL7607526A patent/NL7607526A/xx not_active Application Discontinuation
- 1976-07-07 PT PT65329A patent/PT65329B/pt unknown
- 1976-07-07 RO RO7686862A patent/RO72546A/ro unknown
- 1976-07-07 HU HU76SA2941A patent/HU178720B/hu unknown
- 1976-07-07 CA CA256,493A patent/CA1058219A/en not_active Expired
- 1976-07-07 FR FR7620818A patent/FR2317266A1/fr active Granted
- 1976-07-08 PL PL1976191025A patent/PL102997B1/pl unknown
- 1976-07-08 JP JP51080429A patent/JPS5210211A/ja active Pending
- 1976-07-08 SU SU762380202A patent/SU743578A3/ru active
- 1976-07-08 DE DE2630760A patent/DE2630760C2/de not_active Expired
- 1976-07-08 SE SE7607851A patent/SE7607851L/ not_active Application Discontinuation
- 1976-07-08 BE BE168751A patent/BE843924A/xx not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2853520A (en) * | 1953-11-05 | 1958-09-23 | Univ Ohio State Res Found | Conversion of ethynyl compounds to acetyl compounds |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100674312B1 (ko) * | 2000-09-08 | 2007-01-24 | 에스케이 주식회사 | 아세틸렌 알코올 화합물의 연속 제조방법 |
| CN104549501A (zh) * | 2013-10-28 | 2015-04-29 | 中国石油化工股份有限公司 | 双醋酸亚乙酯法醋酸乙烯催化剂及醋酸乙烯合成方法 |
| CN104844437A (zh) * | 2015-05-12 | 2015-08-19 | 辽宁省石油化工规划设计院有限公司 | 九塔连续精馏法分离溶剂的方法及其装置 |
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